Darcy Dugan: The Extraordinary Life of Australia’s Great Escape Artist
Darcy Dugan during the Nagle Royal Commission into Prisons in 1977-78. Darcy gave evidence as to his experience in Grafton Gaol. On his right is Det. Sgt Bruce Shiels (also known as my Dad)
He escaped from prison vans, court cells, Long Bay Gaol and even through the roof of a moving prison tram. He picked locks, scaled prison walls and once slipped out of a police handcuff in front of his guards.
Long before many in Australia became fascinated with celebrity criminals, there was Darcy Dugan. His name was often spoken about in my house, as Dad was a Detective who had a bit to do with him. Dad even wrote a song about him which went to the tune of “The Green Green Grass of Home”. Dad’s version was called “The Grey, Grey Walls of Gaol”. As a 60’s and 70’s Detective - Dad didn’t hold back in respect to his opinion on career criminals, but the story of Darcy was something that fascinated me.
Whilst he was a crook, and he was a real crook, it is almost impossible not to respect the audacity and ingenuity with which he practised his chosen profession. Darcy didn't merely escape custody, he treated supposedly secure prisons, handcuffs, prison vans and court cells as engineering problems waiting to be solved. He was unquestionably a crook. He was simply exceptionally good at being one.
Lets take a look at Darcy.
Darcy Ezekiel Dugan was a bank robber, convicted criminal and one of the most extraordinary prison escape artists Australia has ever seen. His criminal history was serious. At one point he was sentenced to death. However, it was his almost unbelievable ability to escape from custody that turned Dugan into someone special (at least to me).
His escapes were so unbelievable and courageous, that newspapers reportedly dubbed him the “India-rubber man”, while he later became known as Australia's answer to Houdini.
Darcy was born in Sydney on 29 August 1920 and grew up around Sydney's inner suburbs. His trouble with the law started whilst he was just a youngster. Before he was even a teenager, Dugan was shoplifting around Annandale with other boys, including a young Lennie McPherson, who would later become one of the most notorious figures in Sydney's underworld. He is someone else I would like to blog about sometime.
Darcy soon progressed to juvenile cat burglary and developed something that would become particularly useful throughout his life. Darcy discovered that he had a fascination with locks. In 1937 at the age of 17, he was convicted of stealing from his uncle's hotel and sent to the Gosford Farm Home for Boys. Darcy later described brutal treatment while incarcerated there.
He escaped.
It was the beginning of a pattern that would follow him for decades crime, arrest, imprisonment and escape. Before turning 21, Darcy had already spent time in institutions including Long Bay, Emu Plains, Goulburn and Oberon.
The prison van escape
By 1946, Darcy’s ability to escape from custody was becoming legendary. In January that year, he and another prisoner, Harry Mitchell, were being transported in a prison van from Long Bay to Burwood Court. Darcy had fashioned a screwdriver from a prison fork and clearly the prison escorts hadn’t searched him well enough. He used the screwdriver he made to loosen a ventilation panel in the roof.
The two prisoners then squeezed themselves through the opening in the roof of the prison van and escaped. Darcy was recaptured, however that didnt stop him from doing it again.
Darcy was not your average prisoner. He did it again only weeks later, and this was my favourite of his escapes.
He escaped through the roof of a prison tram
In March 1946, Dugan was being transported between court and prison aboard a prison tram. Back in the 1940’s when trams were still a ‘thing’, there was a tram specifically used to transport prisoners. The corrections guys from the Gaol had somehow missed the news that Darcy was good at making tools from prison utensils. Once again he made some kind of tool and this time rather than a screwdriver, he made a cutting implement.
While the tram travelled through Sydney, he cut a hole in the roof of the tram! As it passed near the Sydney Cricket Ground and Centennial Park area, unbelievably, Darcy climbed through the hole. He escaped through the roof of a moving prison tram. According to the tram driver, he was travelling arount 15 miles an hour and knew nothing until one of the escorting Constables rushed up and said, “Hold it. I think I've lost two of my prisoners. As an ex-cop, I can’t imagine what the poor Constable thought when he discovered Darcy missing. He probably wanted to throw himself out of the tram as well.
The escape caused a sensation. Darcy began to become famous. Newspaper coverage described it as daring, and Darcy acquired the nickname “the India-rubber man.” Police began to dislike Darcy even more. His freedom did not last particularly long. With no food or water, he must have become tired, and he surrendered after approximately 37 hours on the run.
His reputation as an escape artist was now firmly established. So was his career as a criminal.
Long Bay couldn't hold him either
In August 1949, Darcy and his mate William Mears were remanded in custody at Long Bay following a failed robbery. They had been inside for barely any time at all.
Accounts differ slightly on whether it was within half an hour or within two hours of their arrival at ‘The Bay’. Either way, what happened next was extraordinary. Probably using something Darcy had made from a utensil and again probably due to an issue with the ability of staff to search Darcy well enough, the pair picked a lock, got through part of the roof, negotiated the prison walls and escaped from Long Bay.
Then they simply caught a tram back towards the city and they remained free for more than a week before being recaptured.
“Gone to Gowings”
One of the most famous stories associated with Darcy happened later that year. Darcy and Mears were facing substantial prison sentences especially after escaping from Long Bay.
Darcy arranged with Mears to be brought from prison to the Central Court of Petty Sessions where Mears offences were being heard. Apparently Mears called him as a witness. No wonder Police dislike for Darcy was growing, but their ability to search him effectively didnt. See Darcy had another reason for wanting to attend court, and it wasnt to be a witness for his mate Mears.
Darcy was going to escape. During the proceedings, the pair were placed in cells at the Court. You guessed it. With something that was ‘fashioned’ from utensills, they sawed through the bars of the cell and they disappeared into Sydney. According to the story that subsequently became part of Darcy folklore, he left a message behind on the wall:
“Gone to Gowings.”
It was a cheeky reference to the famous Sydney department store advertising slogan. The Australian Dictionary of Biography records the story, although appropriately describes Darcy as having “allegedly” written the words. Whether every detail of the legend is true or not, it was perfectly suited to the public image Darcy had acquired.
He wasnt merely making a laughing stock of the police and the security of prisoners in Sydney. He wasn't merely escaping. He seemed to be having fun doing it.
Then came the bank robbery that nearly cost him his life
In January 1950, Darcy and Mears robbed the Ultimo branch of the Commonwealth Bank. During the robbery, Mears shot and seriously wounded the bank manager. The pair were eventually arrested. In June 1950 they were sentenced to death. Their sentences were subsequently commuted to life imprisonment.
Darcy was sent to Grafton Gaol. It was one of the harshest prisons in New South Wales. And once again, Darcy started thinking about how to get out.
Grafton Gaol – the “Bloodhouse”
Darcy later became an outspoken critic of the treatment of prisoners at Grafton. He described an extraordinarily brutal prison regime, particularly for prisoners classified as unlikely to reform.
While there, Darcy attempted escape on multiple occasions and became involved in an unsuccessful mass breakout. At one stage his treatment became a matter of public concern. In 1953, a petition signed by around 200 people called for Darcy and two other prisoners to be released from solitary confinement.
Another petition signed by thousands of Grafton residents sought an end to the system used to deal with supposedly “intractable” prisoners. Neither succeeded. Darcy nevertheless continued trying to escape.
One account records that he fashioned a key from a steel thimble and used it to unlock his cell. He was caught before completing that escape. At another stage he was discovered hiding in a hole dug beneath a shed in a prison garden.
And while back at Grafton, Darcy reportedly began reading about the world's most famous escape artist - Harry Houdini. He even practised swallowing and regurgitating objects such as knives and forks, an extraordinary skill for a prisoner whose opportunities to obtain tools were understandably limited.
He could even escape from handcuffs
One of the most extraordinary incidents occurred in court in May 1950. Darcy had just been committed for trial and was being moved from the court. He was handcuffed to his mate William Mears and surrounded by two warders and a police officer. Suddenly, Darcy slipped his hand out of the handcuff. He took off with Police chasing him with their pistols drawn.
Darcy crashed through a glass swing door, landed on his shoulder, got back onto his feet and continued running. He almost reached a side exit before a court orderly managed to trap him in the partially opened doorway and restrain him. Perhaps the best part of the contemporary newspaper report was that Police apparently couldn't work out how he had escaped from the standard ratchet handcuff.
Even after they had caught him, Darcy wasn't giving away all his secrets.
Six escapes from custody
Darcy is generally credited with successfully escaping from custody six times, several of them from circumstances designed to be escape-proof. The methods are what make his story so remarkable. He didn't have helicopters waiting outside prison yards ( That story was another awesome one. Anyone who can get someone to fly a helicoptor into a gaol to escape deserves a bloody medal - once he is rearrested of course).
In Darcy’s time there were no mobile phones, GPS devices or sophisticated communications. This little Irish legend escaped using improvised tools, picked locks, manipulated prison infrastructure, climbed through roofs and over walls and apparently possessed an extraordinary ability to identify weaknesses in the systems designed to contain him. He was actually a pretty smart bloke.
The City of Parramatta's history of Darcy describes one Long Bay escape in which he went through a ceiling and roof and over the outer wall in broad daylight, despite an armed guard being only about 30 metres away. Said armed guard probably lost his job in less time that Darcy had been in custody. He had reportedly been imprisoned for only around 25 minutes. For someone running a prison back in the day, Darcy Dugan must have been an absolute nightmare.
But there was another side to Darcy Dugan
Darcy's story became more complicated as he grew older. The story of his young life was also super sad and makes the reader sympathetic to his life choices.
He spent an enormous proportion of his life incarcerated and he became involved in prisoner rehabilitation and prison reform. After being released in the 1960s, he worked with Reverend Ted Noffs at Sydney's Wayside Chapel, became involved in counselling, wrote a play and even acted in a stage production about prison life.
He increasingly spoke publicly about prison brutality and police corruption. Following his later release (yes he went back in again), he again worked in rehabilitation. His experiences also formed the basis of the autobiographical book Bloodhouse, which was published posthumously. The title came from the name associated with Grafton Gaol and the brutal regime Darcy said he experienced there.
He gave evidence at the Nagle Royal Commission in to Prisons in the 1970’s.
And then, incredibly, he ended up in the Court of Criminal Appeal
In 1981, more than four decades after his first periods of detention, Darcy found himself involved in yet another attempted robbery. Police had received information from an informant that he intended to rob a service station at Ashfield. This time they were ready for him.
Police secretly rendered the pistol Darcy was expected to use incapable of firing, supplied the informant with a car fitted with a listening device, positioned officers around the service station and replaced the attendant behind the counter with a police sergeant. The Detective was Dennis Gilligan. A great man. And a brave one in trusting the informant …. not sure if it would have happened these days - however…..
Darcy entered the service station wearing a mask, pointed the pistol at Detective Gilligan who was dressed as the service station attendant and announced that it was a “Hold up.” The man looking down the barrel already knew the gun couldn't fire. Well I am sure that he bloody hoped so. The Judgement in respect to this matter referred to below has a short excerpt from the cross examination of Detective Dennis Gilligan. When it was put to Gilligan that he knew the pistol that Darcy was holding towards him was incapable of firing any bullet, Gilligan responded, “I knew a pistol had been rendered incapable of firing. I was hoping it was the same one.” Very brave Detective in my view.
Anyway - the service station was surrounded by police, and dear Darcy was arrested yet again. He beat the armed robbery charge on technical grounds - on the basis that the ‘victim’ wasnt really a victim and he wasnt in fear as he knew the pistol couldnt fire (that is in very brief summarised terms). However, he was found guilty on alternate charges. His subsequent appeal became R v Dugan [1984] 2 NSWLR 554, an important NSW authority dealing with improper police conduct, entrapment and the discretionary exclusion of evidence.
The Court rejected his appeal.
Perhaps there was some irony in the fact that after decades spent defeating locks, cells, walls, prison vans, trams and handcuffs, this time the police operation finally left Darcy Dugan nowhere to go. Darcy was finally beaten (not literally) and was returned to custody.
Australia's Houdini of the prison system
Darcy Dugan died in 1991, shortly before his 71st birthday. His life cannot be romanticised entirely.
He committed serious crimes. People were endangered and injured during the criminal activity with which he was involved, and he spent decades in prison as a consequence. But even allowing for the mythology that inevitably grew around him, Darcy’s extraordinary talent for escaping custody is difficult not to marvel at.
This poem written by my dad Detective Sergeant Bruce Shiels was written in the 1970’s and definitely doesn’t reflect my views on Darcy. It is included as an interest piece, noting that dad said that he had sung this to Darcy during the time they spent together at the Nagle Royal Commission into Prisons in 1977-1978.
A prison van.
A prison tram.
Court cells.
Long Bay.
Locks. Roofs. Walls. Handcuffs.
Again and again, authorities put Darcy Dugan somewhere from which he was not supposed to be able to escape. Again and again, he found a way out.
For that reason, the name Darcy Dugan occupies a unique place in Australian criminal history. Not simply as a robber or prisoner, but as perhaps Australia's greatest prison escape artist.
Shiels Lawyers
Criminal Law | Traffic Law | AVOs
This article is provided for general information and historical interest and does not constitute legal advice.